As I sit here, waiting patiently for the mailman to (hopefully) deliver a check that a client forgot to mail earlier last month — the check that I need to pay my rent, which is due on the 5th, which means I have to take this check to a check-cashing place in order to convert it to cash faster than the 2-day hold my bank imposes on out-of-state checks — I realize this kind of fiscal conundrum is not uncommon.  Not for me, anyway, and not among other freelancers I talk to.

In fact, truth be told, freelance is a neverending nightmare of financial uncertainty, unreasonable deadlines and tawdry sex.  (And by “tawdry sex,” I really mean “rush fees.”)  Even the best-prepared freelancers inevitably go through lean times, and even the most desperate among us stumble into cash-laden windfalls that momentarily validate our harebrained career choice in the first place.

Thus, if you’re considering hiring a freelancer — or, god forbid, becoming one — here are 5 Ugly Truths you may want to consider before taking the plunge.

1.  You Never Have a Freelancer’s Full Attention

To freelance is to voluntarily forsake steady income in exchange for autonomy.  Therefore, a freelancer’s number one priority is never the client she’s serving now; it’s finding a client to serve next.  Because no matter how important YOU think your project is to your freelancer, that lone project will never pay all her bills — and so she has to keep one eye on the next project down the line; otherwise, she starves.  (And a dead freelancer can’t revise your brochures, so give her a break.)

2.  A Freelancer Never Has Enough Money

That’s because a freelancer never has any money until a client decides to pay her.

Unlike “real” jobs, in which employees are paid regardless of how quickly / well they complete their assigned tasks, a freelancer has no control over how (or when) she gets paid.  Doing the best job or the worst job in the world for a client may not have any impact at all on when that client’s accounting department processes the freelancer’s invoice.  Thus, even though you may have just completed a $5,000 job, it doesn’t mean you’re anywhere close to actually getting that $5,000 (before taxes).  Watch the skies.  (That’s where your checks come from.)

3.  Every Conversation You Have with a Freelancer is Really a Job Interview

But not a job interview in the sense of you hiring them; it’s a case of us evaluating whether or not YOU might be a potential source of income.  Because freelancers instinctively believe EVERYONE they meet is a potential client who might be in desperate need of our services.  Got a bike shop?  I bet you need fliers.  Own a dairy?  You should be on Twitter. Your company manufactures prosthetic legs?  I make how-to videos; we should talk.

4.  The Only Thing a Freelancer Loves More Than Cashing Your Check…

… is firing you as a client.  Not that we enjoy firing clients on a whim, of course — if we did, none of us would ever be employed.  But the act of surviving as a freelancer necessitates withstanding all kinds of asinine, arrogant, miscommunicated and disrespectful bullshit from some clients, who treat freelancers like necessary evils instead of valuable collaborators.  And although we might be willing to withstand your stupidity while we’re building our reputations, trust me — the moment we have enough regular clients to (presumably) pay our bills, we’re all too happy to cease doing business with you.  Because foraging in the wild for a new client is always preferable to dealing with a lousy one.  (And if we wanted to be belittled, insulted and taken for granted, we would have kept our day jobs.)

NOTE:  At this point, you may be asking yourself the question everyone asks a freelancer: “Why would you do that to yourself?”

The reason:

5.  Freelancers Think They’re Better Than You

Not because they’re more talented than you are, which they may be.  And not because they’re better at business than you are, which may also be true, but which we’ll never know because you’re securely employed and they’re not.  And that’s the point: a freelancer is a person who — smart or not, wise or not, sustainable or not — has decided that controlling their own destiny (and preserving what’s left of their own sanity and self-image) is worth giving up a 9-to-5 salary in exchange for a lifetime of shaking the trees for money.  It’s a choice that requires a potent mix of talent, social skills, time management, financial planning, restless nights, infallible willpower and a healthy dose of self-delusion.

Freelancing is as close as a modern desk jockey can get to living a life of occupational adventure without buying a gun.  And for that, we — the freelancers of the world — salute you, the gainfully employed, who provide for us an eternal reminder of the safety and security we’ve decided against.  You enjoy your health insurance and your 401Ks, and we’ll enjoy being able to sleep in ’til noon as long as we keep working ’til 4 AM.

Speaking of which… anybody need a new logo?

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  • That's hilarious. And true. Love #3.
  • This definitely summed up my freelancing experience (5+ years), except for the last point. I just loved freelancing -- I didn't really do it because I thought I was better than full-time workers. And possibly I feel that way because after 5 years and one baby, I caved and went full-time onboard with a firm that had been a client. And after another baby, and a year as a SAHM, I jumped at the first full-time offer I got.

    And now I am hoping Obama's healthcare plan goes through so I can quit and freelance again.

    ciao,
    rpm
  • you hit the nail on the head, Justin. great post.
  • Randie
    I love it, Justin! Now, if I only had a client to fire.

    Randie
  • Reading your post people would start to think that all freelancers are just assholes who have problems with authority... And they'd be right. Great post!
  • Awesome post Justin! We are terrible people, aren't we? :) Last week, I got to cash a check AND fire a client. It felt great.
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